What to Wear to A Highly-Personal, Super Specific Only-to-Me Holiday Fashion Occasion

Help me pick an outfit that says, "I'm not a socialist."
Publish date:
December 24, 2015
clothes, fashion, sweaters, what to wear, in-laws

‘Tis the season to pack our bags and spend several days with the people responsible for birthing and shaping — for better or worse — the psyches of our beloved partners. I’m spending the holidays with my fiancé’s parents this year. Even though I love them to death and they aren’t ultra-conservative, I can’t exactly wear my standard black-on-black on all-black everything to a festive Midwestern family gathering.

As I pack (at the absolute last minute), I am forcing myself to be as exacting and editorial as possible. If you’re also heading home to a home that is not your home filled with inhabitants who hold strange and frightening customs like watching FOX news and praying before meals, join me in smoothing the transition by arming yourself with an arsenal of comfortable, versatile clothes that say, “I will not spar with you about social activism or gun control laws nor will I be resentful for the psychological damage you’ve inflicted upon my chosen life partner. I appreciate you opening your home to me.”

I'm not suggesting that anyone go out and buy a new wardrobe from J. Crew or L.L. Bean or hide their true colors, but in the spirit of the season, let us leave our spiked heels and graphic tee's at home. Let us wear neutral and jewel tones and bow our heads in thanks for these four staples that will allow us to please the eyes — if not the societal standards — of our in-laws.

Now, let us (read: you!) help me decide what to cram into my carry on.

Soft and Muted Knits

When I visit my in-laws, my biggest anxiety is looking too young. My fiancé is ten years older than I am and while his family has been very accepting, I try to avoid any loud indicators of my youth, even though it pains me to leave my much beloved skater skirts at home. You know what isn’t a loud indicator of youth and frivolity? A cowl neck sweater. Beige horizontal stripes. Anything cashmere.


In my day-to-day life, khaki pants are anathema. I think they make me look wide and boring. However, the pair of khaki dress — read: stretchy and fitted — pants in the back of my closet are not black and do not have leather panels or rivets so: Christmas gold.


I keep reiterating comfort is key and there’s no better way to be comfortable than in a pair of flats. As a nice bonus, they take up almost no room in a suitcase — Hello, carry-on friendly footwear! Goodbye, evil airline bag checking fees! — and go with basically everything.


As far as I’m concerned, anything with sequins on it not only diffuses light, but can also diffuse uncomfortable situations. Look, shiny! Look, I come bearing good cheer and a delightful, feminine sensibility!

Before you advise me to not pack a dozen bulky knits OR jump down to the comments to share stories of holiday horror OR vehemently dismiss the notion of "dressing for success" (wherein success equals appeasing the grandparents of your future children), let me impart upon you this final sprig of sage — or, in this case, mistletoe-y — advice: Comfort is key. If you're hunkering down with ultra-conservative in laws, why not slip into something more comfortable — whether it’s a heather gray sweater or a pair of light-wash jeans — than a heated debate on the merits of Donald Trump's foreign policy?